Reactions of 5-(Trialkyl)silylpent-1-en-4-yn-3-ones with Hydrazines: Original Synthetic Routes to Luminescent Substances Containing Azole Motifs

Ivan S. Odin; Kareem V. Gordon; Radik N. Itakhunov; Dmitry M. Gusev; Sergey A. Sokov; Anna V. Vologzhanina; Stanislav A. Grabovskiy; Ilya M. Sosnin; Anton I. Ukolov; Olga I. Orlova; Vladimir A. Lazarenko; Pavel V. Dorovatovskii; Darina D. Darmoroz; Anastasiia O. Piven; Tetiana Orlova; Alexander A. Golovanov

doi:10.1055/s-0043-1763601

Synthesis, Table of Contents

Synthesis 2024; 56(02): 243-266
DOI: 10.1055/s-0043-1763601

paper

Reactions of 5-(Trialkyl)silylpent-1-en-4-yn-3-ones with Hydrazines: Original Synthetic Routes to Luminescent Substances Containing Azole Motifs

Authors

Ivan S. Odin

^aLaboratory of Organic Synthesis and Analysis No. 13, Togliatti State University, 14 Belorusskaya Str., 445020 Togliatti, Russian Federation aleksandgolovanov@yandex.ru
Kareem V. Gordon

^aLaboratory of Organic Synthesis and Analysis No. 13, Togliatti State University, 14 Belorusskaya Str., 445020 Togliatti, Russian Federation aleksandgolovanov@yandex.ru
Radik N. Itakhunov

^aLaboratory of Organic Synthesis and Analysis No. 13, Togliatti State University, 14 Belorusskaya Str., 445020 Togliatti, Russian Federation aleksandgolovanov@yandex.ru
Dmitry M. Gusev

^aLaboratory of Organic Synthesis and Analysis No. 13, Togliatti State University, 14 Belorusskaya Str., 445020 Togliatti, Russian Federation aleksandgolovanov@yandex.ru
Sergey A. Sokov

^aLaboratory of Organic Synthesis and Analysis No. 13, Togliatti State University, 14 Belorusskaya Str., 445020 Togliatti, Russian Federation aleksandgolovanov@yandex.ru
Anna V. Vologzhanina

^bLaboratory of X-ray Diffraction Studies, A. N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Science, 28 Vavilova Str., 119334 Moscow, Russian Federation
Stanislav A. Grabovskiy

^aLaboratory of Organic Synthesis and Analysis No. 13, Togliatti State University, 14 Belorusskaya Str., 445020 Togliatti, Russian Federation aleksandgolovanov@yandex.ru

^cLaboratory of Chemical Kinetics, Ufa Institute of Chemistry, UFRS of the Russian Academy of Science, 71 October Av., 450054 Ufa, Russian Federation
Ilya M. Sosnin

^dInstitute of Advanced Technologies, Togliatti State University, 14 Belorusskaya Str., 445020 Togliatti, Russian Federation
Anton I. Ukolov

^eDepartment of Toxicology, Research Institute of Hygiene, Occupational Pathology and Human Ecology FMBA of Russia, g.p. Kuzmolovskii, 188663, Leningrad Region, Russian Federation
Olga I. Orlova

^eDepartment of Toxicology, Research Institute of Hygiene, Occupational Pathology and Human Ecology FMBA of Russia, g.p. Kuzmolovskii, 188663, Leningrad Region, Russian Federation
Vladimir A. Lazarenko

^fNational Research Centre, Kurchatov Institute, 1 pl. Akad. Kurchatov, 123182 Moscow, Russian Federation
Pavel V. Dorovatovskii

^fNational Research Centre, Kurchatov Institute, 1 pl. Akad. Kurchatov, 123182 Moscow, Russian Federation
Darina D. Darmoroz

^aLaboratory of Organic Synthesis and Analysis No. 13, Togliatti State University, 14 Belorusskaya Str., 445020 Togliatti, Russian Federation aleksandgolovanov@yandex.ru

^gInfochemistry Scientific Center, ITMO University, 9 Lomonosova Str., 191002 Saint-Petersburg, Russian Federation
Anastasiia O. Piven

^aLaboratory of Organic Synthesis and Analysis No. 13, Togliatti State University, 14 Belorusskaya Str., 445020 Togliatti, Russian Federation aleksandgolovanov@yandex.ru

^gInfochemistry Scientific Center, ITMO University, 9 Lomonosova Str., 191002 Saint-Petersburg, Russian Federation
Tetiana Orlova

^aLaboratory of Organic Synthesis and Analysis No. 13, Togliatti State University, 14 Belorusskaya Str., 445020 Togliatti, Russian Federation aleksandgolovanov@yandex.ru

^gInfochemistry Scientific Center, ITMO University, 9 Lomonosova Str., 191002 Saint-Petersburg, Russian Federation
Alexander A. Golovanov∗

^aLaboratory of Organic Synthesis and Analysis No. 13, Togliatti State University, 14 Belorusskaya Str., 445020 Togliatti, Russian Federation aleksandgolovanov@yandex.ru

Abstract

All articles of this category

Dedicated to the Peace that must return once again.

Abstract

On the basis of the selective reactions of hydrazines with trialkylsilyl-substituted cross-conjugated enynones (pent-1-en-4-yn-3-ones) as fundamental building blocks, this work presents the developed common methodology for the synthesis of polysubstituted luminescent derivatives of acetylenic pyrazolines, pyrazoles, and combined polyheterocycles containing structural fragments from pyrazolines, isoxazoles, thiophenes, thiazoles, benzo[d]thiazoles, and benzo[d]imidazoles. In reactions with hydrazine and its monosubstituted aromatic and heteroaromatic derivatives, the mentioned pent-1-en-4-yn-3-ones, containing Me₃Si, Et₃Si, and t-BuMe₂Si groups at the triple bond, give 3-(trialkylsilyl)ethynylpyrazolines. Following stages of desilylation and 1,3-dipolar cycloaddition with nitrile oxides, the 3-(trialkylsilyl)ethynylpyrazolines provide the formation of combined polyheterocyclic derivatives. Thus, a one-pot synthetic route to pyrazoline-containing isoxazoles from cross-conjugated enynones, arylhydrazines, and α-chlorobenzaldoximes has been developed. Some aspects of cyclocondensation mechanism and luminescent properties of synthesized azoles derivatives were examined.

Key words

trialkylsilyl-substituted conjugated enynones - cyclocondensation - chemoselectivity - desilylation - reaction mechanism - polyheterocycles - luminescence - one-pot synthesis

Full Text

References

References

1a Santos NE, Carreira AR. F, Silva VL. M, Braga SS. Molecules 2020; 25: 1364
1b Kumar V, Kaur K, Gupta GK, Sharma AK. Eur. J. Med. Chem. 2013; 69: 735

2a Li G, Cheng Y, Han C, Song C, Huang N, Du Y. RSC Med. Chem. 2022; 13: 1300
2b Fustero S, Sánches-Roselló M, Barrio P, Simón-Fuentes A. Chem. Rev. 2011; 111: 6984

3a Giornal F, Pazenok S, Rodefeld L, Lui N, Vors J.-P, Leroux FR. J. Fluorine Chem. 2013; 152: 2
3b Lambert C. Heterocycles 2007; 71: 1467

4a Tigreros A, Portilla J. RSC Adv. 2020; 10: 19693
4b Karcı F, Karcı F, Demirçalı A, Yamaç M. J. Mol. Liq. 2013; 187: 302

5a Ebenezer O, Shapi M, Tuszynski JA. RSC Adv. 2020; 10: 19693
5b Rostami H, Shiri L, Khani Z. Tetrahedron 2022; 110: 132688
5c Aziz H, Zahoor AF, Ahmad S. J. Chil. Chem. Soc. 2020; 65: 4746
5d Faisal M, Saeed A, Hussain S, Dar P, Larik FA. J. Chem. Sci. 2019; 131: 70
5e Costa RF, Turones LC, Cavalcante KV. N, Júnior IA. R, Xavier CH, Rosseto LP, Napolitano HB, da Silva Castro PF, Neto ML. F, Galvão GM, Menegatti R, Pedrino GR, Costa EA, Rodrig JL. Front Pharmacol. 2021; 12: 666725
5f Alam MJ, Alam O, Naim MJ, Nawaz F, Manaithiya A, Imran M, Thabet HK, Alshehri S, Ghoneim MM, Alam P, Shakeel F. Molecules 2022; 27: 8708

6 Mykhailiuk PK. Chem. Rev. 2021; 121: 1670
7 Ansari A, Ali A, Asif M. Shamsuzzaman, New. J. Chem. 2017; 41: 16

8a Golovanov AA, Odin IS, Gusev DM, Vologzhanina AV, Sosnin IM, Grabovskiy SA. J. Org. Chem. 2021; 86: 7229
8b Odin IS, Chertov AYu, Grigor’eva OB, Golovanov AA. J. Org. Chem. 2022; 87: 5916
8c Itakhunov RN, Odin IS, Gusev DM, Grabovskiy SA, Gordon KV, Vologzhanina AV, Sokov SA, Sosnin IM, Golovanov AA. Org. Biomol. Chem. 2022; 20: 8693

9a Masih A, Agnihotri AK, Srivastava JK, Pandey N, Bhat HR, Singh UP. J. Biochem. Mol. Toxicol. 2020; 35: e22656
9b Roney M, Singh G, Huq AK. M. M, Forid MS, Ishak WM. B. W, Rullah K, Aluwi MF. F. M, Tajuddin SN. Mol. Biotechnol. 2023; 1

10 Lvov AG, Kavun AM, Kachala VV, Lyssenko KA, Shirinian VZ. Org. Biomol. Chem. 2019; 17: 4990

11a Hariprasad S, Srinivasaa HT. Liquid Cryst. 2015; 42: 1612
11b Soria L, Ovejero P, Cano M, Campo JA, Torres MR, Núñez C, Lodeiro C. Dyes Pigments 2014; 110: 159

12a Orrego-Hernández J, Cobo J, Portilla J. ACS Omega 2019; 4: 16689
12b Huang Q, Liu T, Ma D, Liu J, Ren T, Wu W, Zhang J. Dyes Pigments 2022; 198: 110014

13 Vasilevsky SF, Tretyakov EV, Elguero J. Adv. Heterocycl. Chem. 2002; 82: 1
14 Pankova AS, Stukalov AYu, Kuznetsov MA. Org. Lett. 2015; 17: 1826
15 Golubev P, Karpova EA, Pankova AS, Sorokina M, Kuznetsov MA. J. Org. Chem. 2016; 81: 11268
16 Gorja DR, Kumar KS, Kandale A, Meda CL. T, Parsa KV. L, Mukkanti K, Pal M. Bioorg. Med. Chem. Lett. 2012; 22: 2480
17 Fedenok LG, Vasilevsky SF, Shvartsberg MS, Slabuka PA, Izyumov EG. RF Patent 1809607, 1993

18a Torres-Moya I, Martín R, Díaz-Ortiz Á, Prieto P, Carrillo JR. Isr. J. Chem. 2018; 58: 1
18b Arbačiauskienė E, Vilkauskaitė G, Šačkus A, Holzer W. Eur. J. Org. Chem. 2011; 1880
18c Vilkauskaitė G, Šačkus A, Holzer W. Eur. J. Org. Chem. 2011; 5123
18d Counceller CM, Eichman CC, Proust N, Stambuli JP. Adv. Synth. Catal. 2011; 353: 79

19 Belov AI, Terekhova MI, Petrov ES, Vasilevsky SF, Shvartsberg MS. Russ. Chem. Bull. 1992; 41: 398
20 Chen M, Sun N, Xu W, Zhao J, Wang G, Liu Y. Chem. Eur. J. 2015; 21: 18571

21a Wróblewska A, Mlostoń G, Heimgartner H. Tetrahedron: Asymmetry 2015; 26: 1448
21b Golovanov AA, Odin IS, Anoshina OS, Bekin VV, Vologzhanina AV, Voronova ED. Russ. J. Org. Chem. 2017; 53: 1664

22a Ibarra IA, Islas-Jácome A, González-Zamorab E. Org. Biomol. Chem. 2018; 16: 1402
22b Levi L, Müller TJ. J. Eur. J. Org. Chem. 2016; 2907
22c Levi L, Müller TJ. J. J. Chem. Soc. Rev. 2016; 45: 2825
22d Aromí G, Barrios LA, Roubeaub O, Gameza P. Coord. Chem. Rev. 2011; 255: 485

23 Nagarjuna U, Rekha T, Sreenivasulu T, Padmavathi V, Padmaja A. Res. Chem. Intermed. 2018; 44: 4375
24 Radhikaa T, Vijay A, Harinadha BV, Madhavareddy B. Russ. J. Bioorg. Chem. 2020; 46: 429

25a Kuhn R, Henkel K. Justus Liebigs Ann. Chem. 1941; 549: 279
25b Dornow A, Rombusch K. Chem. Ber. 1958; 91: 1841
25c Paul H, Kausmann A. Chem. Ber. 1968; 101: 3700

26a Reimlinger H, Vandewalle JJ. M. Justus Liebigs Ann. Chem. 1968; 720: 117
26b Yoshimatsu M, Kawahigashi M, Honda E, Kataoka T. J. Chem. Soc., Perkin Trans. 1 1997; 696
26c Sokov SA, Odin IS, Zlotski SS, Denisova AG, Golovanov AA. Russ. J. Org. Chem. 2021; 57: 1575

27a Smith CD, Tchabanenko K, Adlington RM, Baldwin JE. Tetrahedron Lett. 2006; 47: 3209
27b Bowling NP, Burrmann NJ, Halter RJ, Hodges JA, McMahon R. J. Org. Chem. 2010; 75: 6382
27c Adamo MF. A, Adlington RM, Baldwin JE, Pritchard GJ, Rathmell RE. Tetrahedron 2003; 59: 2197
27d Ford MF, Walton DR. M. Synthesis 1973; 47
27e Najerá C, Sydnes LK, Yus M. Chem. Rev. 2019; 119: 11110

28a Pankova AS, Golubev PR, Ananyev IV, Kuznetsov MA. Eur. J. Org. Chem. 2012; 5965
28b Botvinnik EV, Blandov AN, Kuznetsov MA. Russ. J. Org. Chem. 2001; 37: 421

29a Finar IF, Okoh E. J. Chem. Soc., Perkin Trans. 1 1973; 2008
29b Shvartsberg MS, Vasilevskii SF, Kostrovskii VG, Kotlyarevskii IL. Chem. Heterocycl. Comp. 1972; 5: 797

30a Brown RF. C, Godfrey PD, Lee SC. Tetrahedron Lett. 1985; 26: 6373
30b Brown RF. C, Eastwood FW, Fallon GD, Lee SC, McGeary RP. Aus. J. Chem. 1994; 41: 991

31 Miller RD, Reiser O. J. Heterocycl. Chem. 1993; 30: 755

32a Golovanov AA, Odin IS, Zlotskii SS. Russ. Chem. Rev. 2019; 88: 280
32b Bondarev GN, Ryzhov VA, Chistokletov VN, Petrov AA. Zh. Org. Khim. 1967; 3: 821

33 Yeom C.-E, Kim MJ, Choi W, Kim BM. Synlett 2008; 565
34 Birkofer L, Ritter A, Uhlenbrauck H. Chem. Ber. 1963; 96: 3280

35a Korzhenevskaya NG, Rybachenko VI, Kovalenko VV, Lyashchuk SN, Redko AN. Russ. J. Org. Chem. 2007; 43: 1475
35b Bagno A, Menna E, Mezzina E, Scorrano G, Spinelli D. J. Phys. Chem. A 1998; 102: 2888

36a Mallesh R, Khan J, Pradhan K, Roy R, Jana NR, Jaisankar P, Ghosh S. ACS Chem. Neurosci. 2022; 13: 2503
36b Das S, Indurthi HK, Asati P, Saha P, Sharma DK. Dyes Pigm. 2022; 199: 110074
36c Xiong J.-F, Li J.-X, Mo G.-Z, Huo J.-P, Liu J.-Y, Chen X.-Y, Wang Z.-Y. J. Org. Chem. 2014; 79: 11619

37 Odin IS, Golovanov AA, Bekin VV, Pisareva VS. Chem. Heterocycl. Compd. 2014; 49: 1687
38 Kaufmann J, Jäckel E, Haak E. ARKIVOC 2019; (iv): 91
39 Ioffe BV, Kuznetsov MA, Potechin AA. Chemistry of Organic Derivatives of Hydrazine . Khimiya; Leningrad: 1979
40 Bishop BC, Brands KM. J, Gibb AD, Kennedy DJ. Synthesis 2004; 43
41 Cohen RD, Wood JS, Lam Y.-H, Buevich AV, Sherer EC, Reibarkh M, Williamson RT, Martin GE. Molecules 2023; 28: 2449
42 Kuciński K, Hreczycho G. Chem. Commun. 2022; 58: 11386

43a Sednev MV, Wurm CA, Belov VN, Hell SW. Bioconjugate Chem. 2013; 24: 690
43b Teng I-T, Bu X, Chung I. Bio-Protoc. 2019; 9: e3375
43c Asiri AM, Al-Amari MM, Khan SA. Polycycl. Aromat. Comp. 2022; 42: 1186

44 Cuadrado P, González-Nogal AM, Valero R. Tetrahedron 2002; 58: 4975
45 Liu K.-C, Shelton BR, Howe RK. J. Org. Chem. 1980; 45: 3916
46 Armarego WL. F, Perrin DD. Purification of Laboratory Chemicals, 3rd ed. Pergamon Press; Oxford: 1988

47a Klimova VA. Basic Micromethods for Analysis of Organic Compounds. Khimiya; Moscow: 1975
47b Gelman NE, Terentieva EA, Shanina TM, Kiparenko LM, Rezl V. Methods of Quantitative Organic Elemental Microanalysis . Khimiya; Moscow: 1987

48 Lazarenko VA, Dorovatovskii PV, Zubavichus YV, Burlov AS, Koshchienko YV, Vlasenko VG, Khrustalev VN. Crystals 2017; 7: 325
49 Kabasch W. Acta Crystallogr., Sect. D 2010; 66: 125
50 Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JA. K, Puschmann H. J. Appl. Crystallogr. 2009; 42: 339
51 Sheldrick GM. Acta Crystallogr., Sect. C 2015; 71: 3
52 Grimme S, Antony J, Ehrlich S, Krieg H. J. Chem. Phys. 2010; 132: 154104
53 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson GA, Nakatsuji H, Li X, Caricato M, Marenich AV, Bloino J, Janesko BG, Gomperts R, Mennucci B, Hratchian HP, Ortiz JV, Izmaylov AF, Sonnenberg JL, Williams-Young D, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski VG, Gao J, Rega N, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Montgomery JA, Peralta JE, Ogliaro F, Bearpark MJ, Heyd JJ, Brothers EN, Kudin KN, Staroverov VN, Keith TA, Kobayashi R, Normand J, Raghavachari K, Rendell AP, Burant JC, Iyengar SS, Tomasi J, Cossi M, Millam JM, Klene M, Adamo C, Cammi R, Ochterski JW, Martin RL, Morokuma K, Farkas O, Foresman JB, Fox DJ. Gaussian 16, Revision A.03 . Gaussian, Inc; Wallingford CT: 2016
54 Scalmani G, Frisch MJ. J. Chem. Phys. 2010; 210: 114110
55 Wiitala KW, Hoye TR, Cramer CJ. J. Chem. Theory Comput. 2006; 2: 1085
56 Horvath KL, Magann NL, Sowden MJ, Gardiner MG, Shernburn MS. J. Am. Chem. Soc. 2019; 141: 19746
57 Attenburrow J, Cameron AF. B, Chapman JH, Evans RM, Hems BA, Jansen AB. A, Walker T. J. Chem. Soc. 1952; 1094
58 CCDC 2269997–2270004 (3a,b,d,5,11a,13c,e,f) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures

Supplementary Material

Supporting Information (PDF)